2,4,6-Trichlorobenzoyl chloride → HCID 11465112, compound

HRID 1784093Notes

Reaction equation

HRID 1784093 reaction equation
[NH2:1][C:2]1[CH:17]=[C:6]2[C:7]3[C:12]([CH2:13][CH2:14][N:5]2[C:4](=[O:18])[N:3]=1)=[CH:11][C:10]([O:15][CH3:16])=[CH:9][CH:8]=3.[Cl:19][C:20]1[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[C:21]=1[C:22](Cl)=[O:23]>C(Cl)(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:19][C:20]1[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[C:21]=1[C:22]([NH:1][C:2]1[CH:17]=[C:6]2[C:7]3[C:12]([CH2:13][CH2:14][N:5]2[C:4](=[O:18])[N:3]=1)=[CH:11][C:10]([O:15][CH3:16])=[CH:9][CH:8]=3)=[O:23]

Participants

5

Reactant 2

HCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 57591096HCID 57591096, compound

Product 1

HCID 11465112HCID 11465112, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of 2-amino-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (7) (40 mg, 0.16 mmol) in CHCl3 (3 mL), DMAP (30.1 mg, 0.24 mmol) and 2,4,6-trichlorobenzoyl chloride (37.5 uL, 0.24 mmol) was added and stirred at 25° C. overnight. After cooling, the mixture was purified on BondElut® SCX (Varian Incorporated) then column chromatography on silica gel (CHCl3/MeOH=50/1 as eluant) to give the title compound (17.1 mg, 24%). 1H-NMR (400 MHz, CDCl3) δ 7.90 (d, 1H), 7.42 (s, 2H), 6.95 (dd, 1H), 6.82 (d, 1H), 4.27 (t, 2H), 3.90 (s, 3.17) and 3.03 (t, 2H); MS (ESI) (M+H)+ 449.

Workup

  1. additionwas added
  2. temperatureAfter cooling
  3. customthe mixture was purified on BondElut® SCX (Varian Incorporated)

Sources & evidence

ORD record
ord-108e0b8006264da1af16c9338792a540
Source dataset
uspto-grants-2009_03
Patent number
US07501512B2

Reaction notes

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